Researcher

David Bulger

Objective

To determine the solubility of 4-pyrenebutanoic acid in a 0.4347:1.000 solution of THF:ethanol or make a 0.6 M solution and confirm the SAMS method with this known solution.

Procedure

A 0.6 M solution of 4-pyrenebutanoic acid in 0.4347:1.000 solution of THF:ethanol was made. The 0.4347:1.000 solution of THF:ethanol was made by adding 869.4 uL of THF to 2 mL of ethanol in a 1-dram vial. The solution was then pipeted into a 2-mL volumetric flask containing 1.2 mmol (346.0 mg) pyrenebutanoic acid up to the 2-mL mark. Thus, a 0.6 M solution was made.

Results

NMR

ONSC101-1
ONSC101-2R
ONSC101-3
Raw JCAMP-DX file for ONSC101-1
Raw JCAMP-DX file for ONSC101-2R
Raw JCAMP-DX file for ONSC101-3

Pictures

ONSC101-1
ONSC101-2
ONSC101-3
ONSC101-4
ONSC101-5
ONSC101-6
ONSC101-7
ONSC101-8
ONSC101-9
ONSC101-10
ONSC101-11
ONSC101-12
ONSC101-13
ONSC101-14

Spreadsheets

[I don't think you properly modified the SAMS calculation cells to account for 2 solvents JCB] I think I fixed the problem.[No not fixed - the volume of each solvent needs to be calculated separately then added JCB] I calculated each solvent separated and weighted their solubility measurements according to the ratio and added them together again.
ONSC101-SAMS
ONSC101-IS - Note: I think I did the calculations wrong for the internal standard.


Solubility

Sample
Solute Peak
Solvents
Internal Standard
SAMS Solubility Measurement (M)
ONSC101-1
2nd Methylene
THF:Ethanol
1,2-dichloroethane
0.51
ONSC101-2R
2nd Methylene
THF:Ethanol
1,2-dichloroethane
0.53
ONSC101-3
2nd Methylene
THF:Ethanol
1,2-dichloroethane
0.51

Discussion

Since the solute didn't dissolve completely, it is surprising that the solubility was measured to be close to 6 M. The solubility measurement of 0.53 M is As the solubility of 4-pyrenebutanoic acid was found in ONSCEXP061 to be 0.06 M in ethanol and in ONSCEXP091 to be 0.55 M in THF, it is also surprising how close the solubility measurements were to the THF measurement of 0.55 M. The internal standard calculations seems to be quite off and should be disregarded until a solution is found.

Conclusion

Previous Calculation method->(The solubility was found to be approximately 0.39 M.) [This number is not calculated correctly so cannot be used JCB]

With the attempt to correct the analyses, the solubility of 4-pyrenebutanoic acid in a 0.4347:1.000 solution of THF:ethanol was measured to be 0.51-0.53 M.

Log

2009-05-27
18:49 Weighed 2-mL volumetric flask (18.119 6 g)
18:50 Added 346.0 mg of 4-pyrenebutanoic acid to volumetric flask
19:06 Weighed volumetric flask (18:465 6 g)
19:08 Photos (ONSC101-1, ONSC101-2)
19:09 Added 869 uL of THF and 2 000 uL of ethanol to 1-dram vial labeled ONSC101-1A
19:13 Vortexed ONSC101-1A for 30 sec
19:14 Photo (ONSC101-3)
19:15 Added solution from ONSC101-1A to volumetric flask up to 2-mL mark
19:17 Vortexed for 10 sec to remove air bubbles
19:18 Added solution from ONSC101-1A to volumetric flask up to 2-mL mark
19:20 Vortexed for 10 sec
19:20 Added solution from ONSC101-1A to volumetric flask up to 2-mL mark
19:21 Vortexed for 10 sec
19:22 Photo (ONSC101-4)
19:22 Parafilmed and added copper wire support
19:25 Began sonication (25 degrees Celsius)
20:00 Removed from sonicator (35 degrees Celsius)
20:02 Photo (ONSC101-5)
20:25 Vortexed for 30 sec
20:26 Photo (ONSC101-6)
20:28 Transferred solution to 1-dram vial
20:31 Photo (ONSC101-7)
20:32 Centrifuged for 3 min
20:37 Photo (ONSC101-8)
20:38 Transferred solution to 1-dram vial
20:40 Photo (ONSC101-9)
20:41 Centrifuged for 3 min
20:46 Photo (ONSC101-10)
20:47 Transferred solution to 1-dram vial
20:48 Photo (ONSC101-11)
20:49 Centrifuged for 3 min
20:55 Photo (ONSC101-12)
20:56 Cleaned NMR tubes, dried, and labeled (101-1, 101-2, 101-3)
21:30 Added 700 uL of DMSO-d6 to three vials labeled 101-1P, 101-2P, 101-3P
21:32 Added 10 uL of 1,2-dichloroethane
21:34 Added 100 uL of saturated solution to vials with pipet in the solution in the vial as dispensing to avoid evaporation
21:37 Vortexed for 30 sec
21:39 Photo (ONSC101-13)
21:40 Transferred solutions to corresponding NMR tubes and parafilmed (NMR tube 101-2 broke while parafilming; transferred solution to another NMR tube labeled 101-2R)
21:52 Photo (ONSC101-14)
22:00 NMR collected for three samples (ONSC101-1, ONSC101-2R, ONSC101-3)

References

1. Solubility of 4-pyrenebutanoic acid in a 0.4347:1.000 solution of THF:ethanol
2. Solubility of 4-pyrenebutanoic acid in non-aqueous solvents
3. ONSCEXP061
4. ONSCEXP091